TW350836B - N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics - Google Patents

N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics

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Publication number
TW350836B
TW350836B TW085106143A TW85106143A TW350836B TW 350836 B TW350836 B TW 350836B TW 085106143 A TW085106143 A TW 085106143A TW 85106143 A TW85106143 A TW 85106143A TW 350836 B TW350836 B TW 350836B
Authority
TW
Taiwan
Prior art keywords
alkyl
hydrogen
phenyl
halo
melatonergics
Prior art date
Application number
TW085106143A
Other languages
Chinese (zh)
Inventor
Daniel J Keavy
Michael F Parker
Ronald J Mattson
Graham Johnson
Original Assignee
Bristol Myers Squibb Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US08/487,306 external-priority patent/US5596019A/en
Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Application granted granted Critical
Publication of TW350836B publication Critical patent/TW350836B/en

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A melatonergic agent having formula I or II, wherein X is halo, hydrogen, C1-4 alkyl or OR5, in which, R5 is hydrogen, C1-4 perfluoro alkyl, C1-4 fluoroalkyl, C1-4 perdeuterium alkyl, C1-10 alkyl, C4-10 alkyl cycloalkyl, C2-10 nitrile alkyl, C3-10 alkoxy carbonyalkyl, C3-10 alkenyl, C3-10 alkynyl, C9-10 phenyl-alkyl, C9-10 phenyl-alkenyl, C9-10 phenyl-alkynyl, C2-10 hydroxy-alkyl, C8-10 phenyl-oxo-alkyl, C7-10 pyridyl alkyl, or C6-10 pyrrolyl alkyl; Y is hydrogen or halo; Z is hydrogen, halo, cyano, phenyl, C7-10 phenyl alkyl or C2-10 alkylamide; R under both circumstances is hydrogen, halo, or C1-4 alkyl; G is divalent ethylene, dimethylene or C1-4 alkyl methylene; R1 is hydrogen, C1-4 alkyl or benzyl; and R2 is C1-6 alkyl, C3-6 cycloalkyl, C2-4 alkoxy alkyl, C1-4 trifluoro methyl alkyl, C2-8 alkyl thioalkyl, or NR3R4 where R3 and R4 independently are selected from hydrogen and C1-4 alkyl, but R3 and R4 may not be hydrogen at the same time.
TW085106143A 1995-06-07 1996-05-23 N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics TW350836B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48663395A 1995-06-07 1995-06-07
US08/487,306 US5596019A (en) 1995-06-07 1995-06-07 N-acyl-cycloalkylamine derivatives as melatonergics

Publications (1)

Publication Number Publication Date
TW350836B true TW350836B (en) 1999-01-21

Family

ID=27048750

Family Applications (1)

Application Number Title Priority Date Filing Date
TW085106143A TW350836B (en) 1995-06-07 1996-05-23 N-acyl-2 aryl cyclopropylmethylamine derivatives as melatonergics

Country Status (23)

Country Link
EP (1) EP0747346B1 (en)
JP (1) JPH08333314A (en)
KR (1) KR100385360B1 (en)
CN (1) CN1068583C (en)
AR (1) AR003139A1 (en)
AT (1) ATE189807T1 (en)
AU (1) AU697028B2 (en)
CA (1) CA2176854A1 (en)
CY (1) CY2221B1 (en)
CZ (1) CZ291380B6 (en)
DE (1) DE69606665T2 (en)
DK (1) DK0747346T3 (en)
ES (1) ES2144666T3 (en)
GR (1) GR3033414T3 (en)
HK (1) HK1014704A1 (en)
HU (1) HUP9601565A3 (en)
IL (1) IL118427A (en)
NO (1) NO311211B1 (en)
NZ (1) NZ286640A (en)
PL (1) PL314671A1 (en)
PT (1) PT747346E (en)
RU (1) RU2162076C2 (en)
TW (1) TW350836B (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR9713690B1 (en) * 1996-12-10 2009-08-11 melatoninergic agents benzodioxole, benzofuran, dihydrobenzofuran and benzodioxane.
US6028112A (en) * 1997-05-23 2000-02-22 Bristol-Myers Squibb Company Spirocyclopropyl fluorenes as melatonergic agents
EP1082115A4 (en) * 1998-06-05 2002-10-24 Bristol Myers Squibb Co Heterocyclic cis cyclopropane derivatives as melatonergic agents
AU4290099A (en) * 1998-06-29 2000-01-17 Mitsubishi-Tokyo Pharmaceuticals, Inc. Process for the preparation of optically active trans-cyclohexylamine compounds
FR2784375B1 (en) * 1998-10-12 2000-11-24 Adir NOVEL CYCLOALKYLENIC CHAIN DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
WO2000021910A2 (en) * 1998-10-14 2000-04-20 Ortho-Mcneil Pharmaceutical, Inc. 1,2-disubstituted cyclopropanes
UY26780A1 (en) 2000-06-15 2002-01-31 Pharmacia Corp CYCLALQUIL AVB3 ANTAGONISTS
US7541055B2 (en) * 2004-09-10 2009-06-02 International Flavors & Fragrances Inc. Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions
US20090203750A1 (en) * 2005-08-24 2009-08-13 Alan Kozikowski 5-HT2C Receptor Agonists as Anorectic Agents
TWI402261B (en) 2006-06-19 2013-07-21 Takeda Pharmaceutical Tricyclic compound and pharmaceutical use thereof
US8835472B2 (en) * 2010-09-02 2014-09-16 Boehringer Ingelheim International Gmbh Compounds, pharmaceutical compositions and uses thereof
IN2014DN10691A (en) 2012-05-18 2015-08-28 Vanda Pharmaceuticals Inc
CN102863341B (en) * 2012-10-22 2014-05-07 南通大学 Chemical synthesis method of (1R, 2S)-2-aryl cyclopropylamine derivative
EP3250549B1 (en) * 2015-01-29 2021-06-23 The Board of Trustees of the University of Illinois Cyclopropylmethanamines as selective 5-ht(2c) receptor agonists
CN105949153B (en) * 2016-05-10 2018-03-02 浙江工业大学 A kind of Ta Simeiqiong synthetic method

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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FR1415997A (en) * 1963-11-05 1965-10-29 Whitefin Holding Sa Phenylcyclopropane derivatives and methods of preparation
US5071875A (en) * 1989-09-25 1991-12-10 Northwestern University Substituted 2-amidotetralins as melatonin agonists and antagonists
JP3007138B2 (en) * 1990-11-27 2000-02-07 ファイザー製薬株式会社 Novel hydroxamic acid and N-hydroxyurea derivatives and compositions thereof
FR2680366B1 (en) * 1991-08-13 1995-01-20 Adir NOVEL ARYLETHYLAMINE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
JP3333510B2 (en) * 1991-10-02 2002-10-15 スミスクライン・ビーチャム・コーポレイション Cyclopentane and cyclopentene derivatives having antiallergic, antiinflammatory and tumor necrosis factor inhibitory activities
US5541228A (en) * 1994-10-14 1996-07-30 Bristol-Myers Squibb Co. Melatonergic agents

Also Published As

Publication number Publication date
ES2144666T3 (en) 2000-06-16
CA2176854A1 (en) 1996-12-08
NO962364L (en) 1996-12-09
JPH08333314A (en) 1996-12-17
EP0747346B1 (en) 2000-02-16
HUP9601565A2 (en) 1997-05-28
HU9601565D0 (en) 1996-08-28
DK0747346T3 (en) 2000-06-05
KR100385360B1 (en) 2003-08-25
NO962364D0 (en) 1996-06-06
PL314671A1 (en) 1996-12-09
ATE189807T1 (en) 2000-03-15
CY2221B1 (en) 2003-04-18
AR003139A1 (en) 1998-07-08
CZ291380B6 (en) 2003-02-12
IL118427A (en) 2000-10-31
CN1143628A (en) 1997-02-26
GR3033414T3 (en) 2000-09-29
EP0747346A3 (en) 1997-11-05
EP0747346A2 (en) 1996-12-11
HUP9601565A3 (en) 1998-03-02
NO311211B1 (en) 2001-10-29
RU2162076C2 (en) 2001-01-20
KR970001306A (en) 1997-01-24
DE69606665T2 (en) 2000-09-21
IL118427A0 (en) 1996-09-12
CN1068583C (en) 2001-07-18
DE69606665D1 (en) 2000-03-23
AU5475996A (en) 1996-12-19
PT747346E (en) 2000-06-30
HK1014704A1 (en) 1999-09-30
CZ163196A3 (en) 1997-06-11
NZ286640A (en) 1998-06-26
AU697028B2 (en) 1998-09-24

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